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Potassium Cryptate of a Macrobicyclic Ligand Featuring a Reducible hexakis(phenylthio)benzene electron‐acceptor site
Author(s) -
Mayor Marcel,
Lehn JeanMarie
Publication year - 1997
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19970800802
Subject(s) - chemistry , benzene , ligand (biochemistry) , titration , acceptor , electron acceptor , potassium , medicinal chemistry , electron donor , crystallography , stereochemistry , inorganic chemistry , photochemistry , organic chemistry , catalysis , biochemistry , physics , receptor , condensed matter physics
The synthesis and structural characterization of the macrobicyclic ligand 1 containing a reducible hexakis‐(phenylthio)benzene electron‐acceptor site is described. It is based on the condensation of the tetraoxa‐diazamacrocycle 3 with a suitably functionalized derivative 4 of hexakis(phenylthio)benzene. Complexation of a potassium cation by 1 gives the corresponding cryptate 2 , with a stability constant of ca. 4000 M −1 as determined by 1 H‐NMR titration in CD 3 CN. The reduction potential of the hexakis(phenylthio)benzene electron‐acceptor site in 2 is shifted by 170 mV towards more positive values with respect to that in 1 by complexation of potassium.